Cationic Palladium Complex-Catalyzed Cyclization-Hydrosilylation of 1,6-Heptadiyne and its Homologs

Synlett

Volumn , Issue 13, 2003, Pages 1997-2000

  Uno, Takanori ^a   Wakayanagi, Shigeru ^a   Sonoda, Yoshiya ^a   Yamamoto, Keiji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

5 , 6 , and 7 membered carbocycle; Cationic palladium complex; Cyclization; Hydrosilylation; , diyne

Indexed keywords

1,6 HEPTADIYNE; ALKANE DERIVATIVE; ALKANEDIYNE; ALKYNE DERIVATIVE; CYCLOALKANE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DIMERIZATION; HYDROSILYLATION; METAL BINDING; REACTION ANALYSIS;

EID: 0242383415     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41494     Document Type: Article

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21. R = 18.2 and 19.3 min), was subjected to a bulb-to-bulb distillation (150-170°C/3 Torr) to give pure 2b as a colorless liquid (0. 207 g, 56% yield), the probable (E)-isomer being hard to be detected within an accuracy of NMR spectra.
22. 13C NMR (67.8 MHz): δ (ppm) = 18.1 (x 3), 42.1, 45.1, 52.8, 56.9, 58.4 (x 3), 112.0, 112.5, 143.7, 158.3, 171.6.
23. 13C NMR: δ = 18.1 (x 3), 20.0, 40.4, 42.7, 52.8, 56.4, 58.3 (x 3), 111.1, 122.0, 144.3, 151.8, and 171.9.
24. 1H NMR: δ = 1.24 (t, J = 6.9 Hz, 9 H), 2.05 (t, J = 2.0 Hz, 3 H), 3.83 (q, J = 6.9 Hz, 6 H), 4.43 (t, J = 2.0 Hz, 2 H), 4.60 (q, J = 2.0 Hz, 2 H), 5.27 (t, J = 2.0 Hz, 1 H), 5.45 (br s, 1 H).
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32. 13C NMR: δ = -5.80, 18.35, 24.31, 25.28, 26.00, 39.28, 39.55, 43.56, 44.01, 52.71, 52.76, 57.68, 58.58 and 58.65 (diastereotopic methylene), 128.25, 131.68, 172.20, 172.51, 180.59, 180.79.